Systematic synthesis of Bis-THF ring cores in annonaceous acetogenins |
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Authors: | Maezaki Naoyoshi Kojima Naoto Tominaga Hiroaki Yanai Minori Tanaka Tetsuaki |
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Institution: | Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan. |
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Abstract: | Systematic synthesis of bis-THF ring cores, synthetic intermediates of adjacent bis-THF annonaceous acetogenins, has been achieved by asymmetric alkynylation and subsequent stereodivergent THF ring formation. The asymmetric alkynylation of alpha-tetrahydrofuranic aldehyde with (S)-3-butyne-1,2-diol derivatives gave good yields of erythro- and threo-adducts with very high diastereoselectivity. These adducts were converted into four types of bis-THF cores via two kinds of one-pot THF ring formation. reaction: see text] |
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